5314 CHISWICK CIRCLE
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    +55 more
    Active
    Single Family Residence

    5314 CHISWICK CIRCLE

    BELLE ISLE, FL, 32812·WINDSOR PLACE PH 01

    MLS# O6438441

    $1,400,000

    4

    Beds

    3

    Baths

    2,487

    Sq Ft

    Description

    THIS LISTING IS FOR THE SALE OF 5314 AND 5308 CHISWICK TOGETHER (the property next door) BY THE SAME OWNER. Rare opportunity to purchase two side-by-side single-family homes, and both have been beautifully maintained. Rare opportunity to own two side-by-side homes in Belle Isle's highly sought-after Windsor Place community, minutes from Orlando International Airport and the Conway Chain of Lakes. Offered together at a slight discount by one seller, this pairing includes a 4-bed/3-bath, 2,487-sq-ft pond-front pool home with no rear neighbors and a 3-bed/2-bath, 2,146-sq-ft pond-view pool home. Both single-story residences feature desirable split-bedroom plans, vaulted ceilings, crown molding, wood-burning fireplaces, and French doors opening to backyard oases with screen-enclosed pools overlooking a tranquil pond, perfect for enjoying those glorious sunsets. The larger home has two ensuite bedrooms, a three-car garage, an extended deck, a covered lanai, a breakfast bar, and stainless-steel GE appliances. The second home shines with a renovated kitchen (granite, 42-inch soft-close cabinets, stainless-steel appliances, breakfast bar), a stunningly remodeled primary bath (freestanding tub, frameless rain-shower, quartz vanities), an oversized pool with raised spa and solar heating, and wrought-iron fencing that borders both properties, with the middle portion left open for easy adventures back and forth. Recent updates across both include new roofs (2022/2023), pool resurfacing (2022), whole-home replumbs (2022/2024), HVAC (2021), water heater (2024), and deck renovations (2022). Schedule your private showing today and experience this rare opportunity firsthand. Individual MLS listing #'s: O6435964 & O6435963. 5314 - All Furniture, decor, artwork, washer, and dryer are NEGOTIABLE. 5308 - Furniture and all items except for those on the rear patio are NEGOTIABLE. 2nd refrigerator DOES NOT CONVEY.

    Property Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1993
    CityBELLE ISLE
    Area32812 - BELLE ISLE
    SubdivisionWINDSOR PLACE PH 01
    StateFL
    CountyOrange
    List Date09/02/2026
    MLS#O6438441
    List Price$1,400,000

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms3
    Full Bathrooms3
    Half Bathrooms0

    Structure

    StyleRanch
    Garage Capacity3
    ParkingDriveway, Garage Door Opener, Open
    Construction MaterialsBlock, Stucco
    RoofShingle
    Foundation DetailsSlab
    FlooringLaminate, Tile
    Private PoolYes
    Patio & PorchCovered, Deck, Screened

    Size & Lot

    Living Area2,487 sqft
    Lot Size11,045 sqft
    Acres0.25
    Lot DescriptionLandscaped, Sidewalk, Paved
    Water FrontNo

    Utilities

    HeatingCentral, Electric
    CoolingCentral Air
    WaterPublic
    SewerPublic Sewer

    Additional Features

    Interior FeaturesCeiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
    Exterior FeaturesPrivate Yard, Rain Gutters, Sidewalk
    AppliancesDishwasher, Electric Water Heater, Microwave, Range, Refrigerator

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About WINDSOR PLACE PH 01

    5314 CHISWICK CIRCLE is located in the WINDSOR PLACE PH 01 community in BELLE ISLE, FL. Part of Orange County.

    The WINDSOR PLACE PH 01 neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$4,798 (2025)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationPaula Butler / Sentry Management
    HOA Fee$346 / annually

    Pet Policy

    Pets AllowedYes

    Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY · Joseph Doher

    Frequently Asked Questions

    What is the asking price for 5314 CHISWICK CIRCLE?

    The listing price for 5314 CHISWICK CIRCLE is $1,400,000.

    How many bedrooms and bathrooms does 5314 CHISWICK CIRCLE have?

    This property features 4 bedrooms and 3 full bathrooms.

    What is the square footage of 5314 CHISWICK CIRCLE?

    The living area is approximately 2,487 square feet.

    What community is 5314 CHISWICK CIRCLE located in?

    This property is located in the WINDSOR PLACE PH 01 community in BELLE ISLE, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 5314 CHISWICK CIRCLE built?

    This property was built in 1993.

    What schools are near 5314 CHISWICK CIRCLE?

    BELLE ISLE is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 5314 CHISWICK CIRCLE?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-09-05. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.